DE4427979A1 - Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung - Google Patents
Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre VerwendungInfo
- Publication number
- DE4427979A1 DE4427979A1 DE4427979A DE4427979A DE4427979A1 DE 4427979 A1 DE4427979 A1 DE 4427979A1 DE 4427979 A DE4427979 A DE 4427979A DE 4427979 A DE4427979 A DE 4427979A DE 4427979 A1 DE4427979 A1 DE 4427979A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- aryl
- radical
- substituted
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 230000027455 binding Effects 0.000 claims abstract description 13
- 238000009739 binding Methods 0.000 claims abstract description 13
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 12
- 210000004027 cell Anatomy 0.000 claims abstract description 5
- 210000000988 bone and bone Anatomy 0.000 claims abstract description 4
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- 210000002997 osteoclast Anatomy 0.000 claims abstract description 4
- -1 cyano, hydroxy Chemical group 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000003254 radicals Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 150000005840 aryl radicals Chemical class 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 16
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- 150000002829 nitrogen Chemical class 0.000 claims description 2
- 239000002831 pharmacologic agent Substances 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 27
- 210000001772 blood platelet Anatomy 0.000 abstract description 15
- 230000002776 aggregation Effects 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 4
- 238000011282 treatment Methods 0.000 abstract description 3
- 201000009030 Carcinoma Diseases 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229940012952 fibrinogen Drugs 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 108010049003 Fibrinogen Proteins 0.000 description 7
- 102000008946 Fibrinogen Human genes 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 7
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001413 amino acids Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
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- 229960004072 thrombin Drugs 0.000 description 3
- UXBIXOXDACBTDG-UHFFFAOYSA-N 1-adamantyl radical Chemical compound C1C(C2)CC3C[C]1CC2C3 UXBIXOXDACBTDG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
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- 125000004341 endo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])* 0.000 description 2
- 125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
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- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- FLZZNZJENFNFOJ-UHFFFAOYSA-N methyl n'-nitrocarbamimidothioate Chemical compound CSC(N)=N[N+]([O-])=O FLZZNZJENFNFOJ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- IYJMSDVSVHDVGT-PEQKVOOWSA-N metildigoxin Chemical compound O1[C@H](C)[C@@H](OC)[C@@H](O)C[C@@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O IYJMSDVSVHDVGT-PEQKVOOWSA-N 0.000 description 1
- 229960003746 metildigoxin Drugs 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
- 229960004027 molsidomine Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229960001132 naftidrofuryl Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960003642 nicergoline Drugs 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229960004570 oxprenolol Drugs 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 description 1
- 229960002035 penbutolol Drugs 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CYXKNKQEMFBLER-UHFFFAOYSA-N perhexiline Chemical compound C1CCCNC1CC(C1CCCCC1)C1CCCCC1 CYXKNKQEMFBLER-UHFFFAOYSA-N 0.000 description 1
- 229960000989 perhexiline Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 201000011461 pre-eclampsia Diseases 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000009863 secondary prevention Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 108091007466 transmembrane glycoproteins Proteins 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical compound C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
- 108010047303 von Willebrand Factor Proteins 0.000 description 1
- 102100036537 von Willebrand factor Human genes 0.000 description 1
- 229960001134 von willebrand factor Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4427979A DE4427979A1 (de) | 1993-11-15 | 1994-08-08 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| HU9601300A HU223806B1 (hu) | 1993-11-15 | 1994-10-24 | Szubsztituált 5-tagú heterociklusos vegyületek, ezek előállítása és alkalmazása |
| KR1019960702512A KR100402192B1 (ko) | 1993-11-15 | 1994-10-24 | 치환된5원환헤테로사이클,이의제조방법및이를포함하는약제학적제제 |
| CA002169643A CA2169643A1 (en) | 1993-11-15 | 1994-10-24 | Substituted 5-ring heterocycles, their preparation and their use |
| US08/640,895 US5981492A (en) | 1993-11-15 | 1994-10-24 | Substituted 5-membered ring heterocycles, their preparation and their use |
| PT94930215T PT729460E (pt) | 1993-11-15 | 1994-10-24 | Heterociclos pentagonais substituidos, sua preparacao e utilizacao |
| DK94930215T DK0729460T3 (da) | 1993-11-15 | 1994-10-24 | Substituerede 5-ring-heterocykler, deres fremstilling og anvendelse |
| CZ19961162A CZ292573B6 (cs) | 1993-11-15 | 1994-10-24 | Substituované pětičlenné heterocykly, způsob jejich výroby a jejich použití v léčivech |
| AU79397/94A AU693811B2 (en) | 1993-11-15 | 1994-10-24 | Substituted 5-ring heterocycles, their preparation and their use |
| SK585-96A SK284471B6 (sk) | 1993-11-15 | 1994-10-24 | Substituované päťčlenné heterocykly, spôsob ich výroby, ich medicínske použitie, farmaceutický prostriedok s ich obsahom a spôsob jeho výroby |
| RU96113118/04A RU2151143C1 (ru) | 1993-11-15 | 1994-10-24 | Замещенные 5-членные гетероциклы, способ их получения, фармацевтическая композиция |
| PCT/EP1994/003491 WO1995014008A1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
| EP94930215A EP0729460B1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
| JP51417695A JP3813983B2 (ja) | 1993-11-15 | 1994-10-24 | 置換された５環状ヘテロ環類、その製造方法及びその使用方法 |
| DE59410120T DE59410120D1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
| PL94314306A PL180906B1 (pl) | 1993-11-15 | 1994-10-24 | Związki heterocykliczne o 5-członowym pierścieniu, sposób ich wytwarzania i preparat farmaceutyczny |
| ES94930215T ES2176261T3 (es) | 1993-11-15 | 1994-10-24 | Heterociclos de 5 eslabones en el anillo sustituidos, su preparacion y su empleo. |
| CN94194043A CN1069316C (zh) | 1993-11-15 | 1994-10-24 | 取代的5－元杂环,它们的制备方法及用途 |
| AT94930215T ATE217615T1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
| IL11162294A IL111622A (en) | 1993-11-15 | 1994-11-14 | Substituted 5-membered ring heterocycles their preparation and pharmaceutical compositions containing them |
| TW083111713A TW326040B (en) | 1993-11-15 | 1994-12-13 | Substituted 5-membered ring heterocycles, their preparation and their use |
| FI962043A FI113265B (fi) | 1993-11-15 | 1996-05-14 | Menetelmä uusien, verihiutaleiden aggregaatiota estävien 2,5-dioksoimidatsolidinyylijohdannaisten valmistamiseksi |
| US09/362,363 US6191282B1 (en) | 1993-11-15 | 1999-07-28 | Substituted 5-membered ring heterocycles comprising a bicyclic or tricyclic group their preparation and their use |
| CY0300083A CY2385B1 (en) | 1993-11-15 | 2003-11-11 | Substituted 5-ring heterocycles, their preparationand their use. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4338944A DE4338944A1 (de) | 1993-11-15 | 1993-11-15 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4427979A DE4427979A1 (de) | 1993-11-15 | 1994-08-08 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4427979A1 true DE4427979A1 (de) | 1996-02-15 |
Family
ID=25931237
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4427979A Withdrawn DE4427979A1 (de) | 1993-11-15 | 1994-08-08 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE59410120T Expired - Lifetime DE59410120D1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59410120T Expired - Lifetime DE59410120D1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US5981492A (cs) |
| EP (1) | EP0729460B1 (cs) |
| JP (1) | JP3813983B2 (cs) |
| KR (1) | KR100402192B1 (cs) |
| CN (1) | CN1069316C (cs) |
| AT (1) | ATE217615T1 (cs) |
| AU (1) | AU693811B2 (cs) |
| CA (1) | CA2169643A1 (cs) |
| CY (1) | CY2385B1 (cs) |
| CZ (1) | CZ292573B6 (cs) |
| DE (2) | DE4427979A1 (cs) |
| DK (1) | DK0729460T3 (cs) |
| ES (1) | ES2176261T3 (cs) |
| FI (1) | FI113265B (cs) |
| HU (1) | HU223806B1 (cs) |
| IL (1) | IL111622A (cs) |
| PL (1) | PL180906B1 (cs) |
| PT (1) | PT729460E (cs) |
| RU (1) | RU2151143C1 (cs) |
| SK (1) | SK284471B6 (cs) |
| TW (1) | TW326040B (cs) |
| WO (1) | WO1995014008A1 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996033976A1 (de) * | 1995-04-28 | 1996-10-31 | Hoechst Aktiengesellschaft | Hydantoinderivate als zwischenprodukte für pharmazeutische wirkstoffe |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4427979A1 (de) | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| JP3895792B2 (ja) * | 1995-12-08 | 2007-03-22 | プロスケリア・エス・ア・エス | 骨形成促進剤 |
| ES2171768T3 (es) * | 1996-03-20 | 2002-09-16 | Hoechst Ag | Inhibidores de la resorcion osea y antagonistas de receptores de vitronectina. |
| DE19622489A1 (de) * | 1996-06-05 | 1997-12-11 | Hoechst Ag | Salze des 3-(2-(4-(4-(Amino-imino-methyl)-phenyl)-4- methyl-2,5-dioxo-imidazolidin-1-yl)-acetylamino)-3- phenyl-propionsäure-ethylesters |
| DE19624604A1 (de) * | 1996-06-20 | 1998-01-02 | Hoechst Ag | Verfahren zur Herstellung chiraler, nicht racemischer (4-Aryl-2,5-dioxoimidazolidin-1-yl)essigsäuren |
| DE19629816A1 (de) | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19629817A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Imino-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19647381A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | Neue Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| KR100697959B1 (ko) * | 1996-11-15 | 2007-07-09 | 훽스트 게엠베하 | 백혈구부착의억제제및vla-4길항제로서의헤테로사이클 |
| DE19647380A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-Ring-Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| PL323130A1 (en) | 1996-11-15 | 1998-05-25 | Hoechst Ag | Application of heterocyclic compounds in production of a pharmaceutic agent, novel heterocyclic compounds and pharmaceutic agent as such |
| DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19741873A1 (de) * | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19751251A1 (de) | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate |
| DE19821483A1 (de) * | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19922462A1 (de) | 1999-05-17 | 2000-11-23 | Aventis Pharma Gmbh | Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US6624187B1 (en) * | 2000-06-12 | 2003-09-23 | Health Research, Inc. | Long wave length absorbing bacteriochlorin alkyl ether analogs |
| DE10111877A1 (de) * | 2001-03-10 | 2002-09-12 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE10137595A1 (de) | 2001-08-01 | 2003-02-13 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung und ihre Verwendung |
| JP2007514742A (ja) * | 2003-12-18 | 2007-06-07 | アストラゼネカ アクチボラグ | トロンビンの阻害薬として有用な新規５，６−ジヒドロピリジン−２−オン化合物 |
| CN107383147A (zh) * | 2017-07-14 | 2017-11-24 | 广东食品药品职业学院 | 一种β‑谷甾醇与依帕司他偶联物及其制备方法和用途 |
| WO2019200202A1 (en) * | 2018-04-12 | 2019-10-17 | Morphic Therapeutic, Inc. | Antagonists of human integrin (alpha4)(beta7) |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| BR112022007284A2 (pt) | 2019-10-16 | 2022-07-05 | Morphic Therapeutic Inc | Inibição de integrina humana alpha-4 beta-7 |
| CN117800921B (zh) * | 2024-02-28 | 2024-06-11 | 南京市鸿舜医药科技有限公司 | 一种咪唑烷二酮类hdac抑制剂、制备方法及应用 |
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|---|---|---|---|---|
| US3300510A (en) * | 1964-03-06 | 1967-01-24 | American Home Prod | Hydantoins |
| DE2714655A1 (de) * | 1977-04-01 | 1978-10-05 | Bayer Ag | Verfahren zur herstellung von hydantoinen |
| EP0006352A1 (en) * | 1978-06-15 | 1980-01-09 | Beecham Group Plc | Hydantoins and thiohydantoins, process for their preparation and pharmaceutical compositions containing them |
| GB2032419B (en) * | 1978-09-05 | 1983-01-19 | Wellcome Found | Hydantoin prostaglandin analogues |
| CA2008116C (en) * | 1989-02-23 | 2001-11-20 | Thomas Weller | Glycine derivatives |
| DE4009506A1 (de) * | 1990-03-24 | 1991-09-26 | Hoechst Ag | Hydantoinderivate |
| WO1992019595A1 (en) * | 1991-05-07 | 1992-11-12 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE4126277A1 (de) * | 1991-08-08 | 1993-02-11 | Cassella Ag | Hydantoinderivate |
| DE4207254A1 (de) * | 1992-03-07 | 1993-09-09 | Cassella Ag | 4-oxo-2-thioxoimidazolidin-derivate |
| DE4213634A1 (de) * | 1992-04-24 | 1993-10-28 | Cassella Ag | 2,4-Dioxo-imidazolidin-Derivate |
| DE4224414A1 (de) * | 1992-07-24 | 1994-01-27 | Cassella Ag | Phenylimidazolidin-derivate, ihre Herstellung und ihre Verwendung |
| DE4301747A1 (de) * | 1993-01-23 | 1994-07-28 | Cassella Ag | Substituierte Aminoverbindungen, ihre Herstellung und ihre Verwendung |
| DE4308034A1 (de) | 1993-03-13 | 1994-09-15 | Cassella Ag | Neue Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4309867A1 (de) | 1993-03-26 | 1994-09-29 | Cassella Ag | Neue Harnstoffderivate, ihre Herstellung und Verwendung |
| DE4427979A1 (de) | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
-
1994
- 1994-08-08 DE DE4427979A patent/DE4427979A1/de not_active Withdrawn
- 1994-10-24 WO PCT/EP1994/003491 patent/WO1995014008A1/de active IP Right Grant
- 1994-10-24 EP EP94930215A patent/EP0729460B1/de not_active Expired - Lifetime
- 1994-10-24 RU RU96113118/04A patent/RU2151143C1/ru not_active IP Right Cessation
- 1994-10-24 SK SK585-96A patent/SK284471B6/sk unknown
- 1994-10-24 PL PL94314306A patent/PL180906B1/pl not_active IP Right Cessation
- 1994-10-24 DK DK94930215T patent/DK0729460T3/da active
- 1994-10-24 DE DE59410120T patent/DE59410120D1/de not_active Expired - Lifetime
- 1994-10-24 CA CA002169643A patent/CA2169643A1/en not_active Abandoned
- 1994-10-24 AT AT94930215T patent/ATE217615T1/de not_active IP Right Cessation
- 1994-10-24 CN CN94194043A patent/CN1069316C/zh not_active Expired - Fee Related
- 1994-10-24 PT PT94930215T patent/PT729460E/pt unknown
- 1994-10-24 AU AU79397/94A patent/AU693811B2/en not_active Ceased
- 1994-10-24 ES ES94930215T patent/ES2176261T3/es not_active Expired - Lifetime
- 1994-10-24 CZ CZ19961162A patent/CZ292573B6/cs not_active IP Right Cessation
- 1994-10-24 HU HU9601300A patent/HU223806B1/hu not_active IP Right Cessation
- 1994-10-24 KR KR1019960702512A patent/KR100402192B1/ko not_active Expired - Fee Related
- 1994-10-24 US US08/640,895 patent/US5981492A/en not_active Expired - Lifetime
- 1994-10-24 JP JP51417695A patent/JP3813983B2/ja not_active Expired - Fee Related
- 1994-11-14 IL IL11162294A patent/IL111622A/xx not_active IP Right Cessation
- 1994-12-13 TW TW083111713A patent/TW326040B/zh active
-
1996
- 1996-05-14 FI FI962043A patent/FI113265B/fi not_active IP Right Cessation
-
1999
- 1999-07-28 US US09/362,363 patent/US6191282B1/en not_active Expired - Fee Related
-
2003
- 2003-11-11 CY CY0300083A patent/CY2385B1/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996033976A1 (de) * | 1995-04-28 | 1996-10-31 | Hoechst Aktiengesellschaft | Hydantoinderivate als zwischenprodukte für pharmazeutische wirkstoffe |
| US5939556A (en) * | 1995-04-28 | 1999-08-17 | Hoechst Aktiengesellschaft | Hydantoin compounds, salts thereof, processes for their preparation, and processes for preparing pharmaceutically active compounds comprising them |
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